Middletown, NY Homes for Sale under $400,000

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  /25

  $375,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  71 Commonwealth Ave, Middletown, NY 10940

  Welcome to the perfect blend of comfort, character, and location. Nestled in the vibrant heart of Middletown, NY—just 70 miles from NYC—this beautifully updated home offers a peaceful retreat without sacrificing proximity. Whether you’re commuting for work or play, nearby transportation options, including the Metro-North train and major highways, make travel to the city a breeze. And when you're

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (845) 436-3953

  71 Commonwealth Ave, Middletown, NY 10940
• Explore Middletown

• 

  

  

  /21

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,639 Sq Ft

  389 Fair Oaks Rd, Middletown, NY 10940

  Beautiful contemporary capecod offers 3 to 4 bedrooms and 2 full bathrooms. Open kitchen/dining room with stainless steel appliances, brand new stove, microwave is only 1 year old. Large patio in front of the house. Ceramic tiles and hardwood floors throughout. Primary bedroom has a walk-in closet. First floor bedroom makes an ideal guest room, or for someone that doesn't want to do do stairs.

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 208-1615

  389 Fair Oaks Rd, Middletown, NY 10940
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  /38

  $300,000

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft

  1538 Route 211 W, Middletown, NY 10940

  Escape to this beautiful farmhouse on 1.6 acres in the Minisink School District! With 2 bedrooms and 2 bathrooms, this home offers cozy living with a bonus—two extra rooms perfect for a hobby space, gym, or office. The backyard seamlessly meets a tranquil stream, providing a peaceful setting for relaxation or outdoor activities. Whether you're an investor or looking for a new place to call home,

  

  John Olivero

  Keller Williams Realty

  (329) 219-1476

  1538 Route 211 W, Middletown, NY 10940
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  /11

  $350,000

  • 4 Beds
  • 2.5 Baths
  • 2,088 Sq Ft

  19 Randall Terrace, Middletown, NY 10940

  Looking for all investors who want to buy now and get the process started in order to work on the exterior before the cold weather begins. All reasonable offers will be considered. Home features an eat in kitchen with breakfast nook, diningroom, and large step down livingroom on first floor with fireplace. Upstairs find a primary bedroom suite with separate bath. Down the hall is three more

  

  Lynelle Alessi

  Keller Williams Hudson Valley

  (329) 216-0798

  19 Randall Terrace, Middletown, NY 10940
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  /40

  $355,000

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft

  29 Red Barn Ln, Middletown, NY 10940

  Welcome to 29 Red Barn Lane, a beautiful home tucked away in one of Middletown’s most desirable neighborhoods. This property combines comfort, style, and convenience—perfect for today’s lifestyle.Step inside and you’ll be greeted by a warm, open layout designed for both everyday living and entertaining. The spacious living room flows seamlessly into a bright dining area and a modern

  Kevin Grier Keller Williams Hudson Valley

  29 Red Barn Ln, Middletown, NY 10940
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  /38

  $389,900

  • 3 Beds
  • 2.5 Baths
  • 1,643 Sq Ft

  100 Excelsior Ave, Middletown, NY 10940

  Welcome home to this 3 bedroom, 2.5 bath colonial tucked away on a quiet side street in the outskirts of Middletown! This home offers a comfortable layout starting with the main floor living room that seamlessly flows into an open kitchen and dining area - perfect for everyday living and entertaining. Here you will also find the convenience of a half bath, laundry room, direct access to a

  Melinda White Keller Williams Realty

  100 Excelsior Ave, Middletown, NY 10940
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  /32

  $385,000

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft

  5 Perrins Mews Unit 6, Middletown, NY 10940

  THE MOST VERSATILE FLOOR PLAN IN THE COMMUNITY! OFFERING THE POTENTIAL FOR ONE-LEVEL LIVING!!! Turn-key and move-in ready, this special home welcomes you with a first-floor primary suite complete with a connected full bath—a rare and highly desirable feature as this home could provide ease of living for those looking to avoid stairs. Extra wide doorways to assist with maneuverability! The

  Frank Muccari Cronin & Company Real Estate

  5 Perrins Mews Unit 6, Middletown, NY 10940
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  /38

  $359,000

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft

  33 Red Barn Ln, Middletown, NY 10940

  Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhouse perfectly situated near schools, shopping, and major highways for an easy commute. Pride of ownership is evident throughout with spacious living areas, a functional layout, and thoughtful updates. The finished lower level offers additional living space, while the 1-car garage provides convenience and storage. Set at the end of

  Donna Reese Keller Williams Hudson Valley

  33 Red Barn Ln, Middletown, NY 10940
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  /28

  $375,000

  • 3 Beds
  • 1.5 Baths
  • 1,856 Sq Ft

  53 Fair Oaks Rd, Middletown, NY 10940

  Welcome to this charming ranch-style home set on 4.8 acres, consisting of two lots (2.3 and 2.5 acres), offering comfort, convenience, and room to enjoy both inside and out. This 3-bedroom, 1.5-bath home features a bright and inviting eat-in kitchen with granite countertops, perfect for casual meals or gatherings. This home comes equipped with central air conditioning and a whole-house generator

  Karen Green-Nelson Coldwell Banker Realty

  53 Fair Oaks Rd, Middletown, NY 10940
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  /34

  $384,000

  • 2 Beds
  • 2.5 Baths
  • 1,677 Sq Ft

  28 Pinto Rd W, Middletown, NY 10941

  Welcome to this stunning, better-than-new townhome located in the highly sought-after community of Liberty Commons. Just one year young, this impeccably maintained residence offers the perfect blend of modern luxury, comfort, and convenience. Step inside to discover a light-filled open layout featuring gleaming hardwood floors on the main level and plush carpeting upstairs. The designer kitchen

  Juan Bautista Keller Williams Realty

  28 Pinto Rd W, Middletown, NY 10941
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  /25

  $379,999

  • 3 Beds
  • 1.5 Baths
  • 1,132 Sq Ft

  408 County Route 22, Middletown, NY 10940

  MINISINK SCHOOLS-Welcome home to 408 County Route 22, a charming raised ranch in the heart of the Hudson Valley. This home is ready for your personal touch and updates, with a list of solid improvements that give you a head start. Inside, the home features a traditional raised ranch layout with living, dining and kitchen spaces on the main level, plus bedrooms and baths awaiting your vision. The

  Glenn Ramcharitar Rita Levine Real Estate

  408 County Route 22, Middletown, NY 10940
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  /45

  $353,000

  • 3 Beds
  • 1.5 Baths
  • 1,564 Sq Ft

  38 Wilson St, Middletown, NY 10940

  Welcome to 38 Wilson where charm, space, and potential come together.This 3-bedroom, 1.5-bath split-level home offers a fresh start with newly painted interiors and a layout full of possibility. Step inside to soaring cathedral ceilings and a bright open-concept kitchen, perfect for both everyday living and entertaining. Upstairs features three generously sized bedrooms and a full bathroom.

  Pete Koutros Keller Williams Hudson Valley

  38 Wilson St, Middletown, NY 10940
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  /17

  $360,000

  • 4 Beds
  • 2 Baths
  • 1,796 Sq Ft

  24 Edinburgh Rd, Middletown, NY 10941

  Looking for something different? This spacious 4 bedroom 2 full bath contemporary raised ranch in the Town Of Wallkill just may be what you are looking for ! Open living room with cathedral ceilings & hardwood flooring. First floor primary bedroom & primary bath. Upper level has hardwood flooring through out with 3 bedrooms & a full bath. Family room on lower level. Rear deck overlooking your

  Ernie Acampora River Realty Services, Inc.

  24 Edinburgh Rd, Middletown, NY 10941
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  /48

  $399,999

  • 3 Beds
  • 3 Baths
  • 2,236 Sq Ft

  19-21 Wilson St, Middletown, NY 10940

  Check out this spacious 3 bedroom, 3 full bathroom Ranch-style home nestled in the heart of the City of Middletown within the Middletown School District. Designed with comfort and functionality in mind, this home offers plenty of room for everyday living, entertaining, and multi-generational needs. Step inside to a warm and inviting layout featuring a large eat-in kitchen with abundant oak

  JOHN SCARANO Keller Williams Realty

  19-21 Wilson St, Middletown, NY 10940
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  /41

  $325,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,256 Sq Ft

  138 Camp Orange Rd, Middletown, NY 10941

  Welcome to this 3-bedroom, 1-bath ranch nestled on 1.4 peaceful acres, offering both privacy and opportunity. With its single-level living, this home is a great fit for first-time buyers, downsizers, or anyone ready to put their personal touch on a property with solid bones. Inside, you’ll find an inviting layout ready for updates—walls, ceilings, and flooring await your vision to transform this

  Annmarie Kovacs Howard Hanna Rand Realty

  138 Camp Orange Rd, Middletown, NY 10941
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  /38

  $325,500 Open Sun 2PM - 4PM

  • 4 Beds
  • 1.5 Baths
  • 1,496 Sq Ft

  8 Park Row, Middletown, NY 10941

  Welcome to this beautifully renovated, well-maintained, and completely move-in ready 4-bedroom, 1.5-bath townhouse in Middletown, NY. Offering a bright and inviting layout, this home features modern updates throughout and plenty of space for comfortable living. The main level features a spacious eat-in kitchen with a generous pantry and a thoughtfully designed and efficient kitchen complete with

  Vanessa Wight BHG Real Estate Green Team

  8 Park Row, Middletown, NY 10941
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  /33

  $399,900

  • 1 Bed
  • 1 Bath
  • 1,088 Sq Ft

  727 Route 17m, Middletown, NY 10940

  A Truly Unique Opportunity – Live, Work, or Both!Welcome to a property that perfectly blends charm, function, and versatility. This special offering is not only a wonderful place to call home but also provides incredible potential to operate your own business—all in a convenient, easily accessible location.Currently configured as a single-family residence with mixed-use potential, this

  Frank Muccari Cronin & Company Real Estate

  727 Route 17m, Middletown, NY 10940
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  /25

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  136 & 140 Gillen Rd, Middletown, NY 10940

  Affordable 3-bedroom ranch in a nice location just off Route 17M . This home features a metal roof, central A/C and Leased solar panels. Solar panels have a transferrable lease and provide very low electric bills. This sale includes the 2 lots. The home 136 Gillen lot is 4-2-7 is .55 acres and the additional lot 140 Gillen lot is 4-2-8 .18 acre. Both lots total .74 combined. This is an as is

  Karie Boniface Cronin & Company Real Estate

  136 & 140 Gillen Rd, Middletown, NY 10940
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  /18

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  41 California Ave, Middletown, NY 10940

  Well maintained 2-Family home with a beautiful back yard for sale in Middletown. An excellent investment opportunity with the ability to live in one unit and rent the other unit. Large backyard is perfect to relaxing and entertaining. Unit One - Enter through the enclosed front porch to a sunny living room with hardwood flooring and plenty of windows. The dining room is nice and bright with

  Joseph Paoli Howard Hanna Rand Realty

  41 California Ave, Middletown, NY 10940
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  /35

  $350,000

  • 2 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  1 Lake Ridge Dr, Middletown, NY 10940

  Nestled in the sought-after Lake Ridge at Water’s Edge community in Middletown, NY, this beautifully maintained end-unit townhouse offers a perfect blend of comfort, style, and convenience. Featuring 2 bedrooms and 1.5 baths, the home boasts modern touches throughout, including luxury vinyl flooring, recessed LED lighting, and a cozy gas fireplace. The kitchen is equipped with stainless steel

  Colin Seitz RE/MAX Benchmark Realty Group

  1 Lake Ridge Dr, Middletown, NY 10940
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  /24

  $349,999

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  53 Richmond Place, Middletown, NY 10940

  Beautifully renovated two-story home in Orange County! Featuring a brand-new kitchen with granite countertops and modern appliances, stunning flooring throughout, a first-floor laundry area, and a cozy covered wrap-around porch! Upstairs, you'll find three bedrooms, a full bath, and a walk-up attic for convenient storage. The yard is mostly fenced, offering safety for kids and pets, with an

  Kelly Roebuck Curasi Realty, Inc.

  53 Richmond Place, Middletown, NY 10940
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  /2

  $350,000

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft

  8 Hill Rd, Middletown, NY 10941

  Looking for a home you can make your own without breaking the bank? This 924 sq ft ranch style home on 4 private acres with direct Wallkill River access is a rare opportunity! This home needs some cleanup and finishing touches inside. You could move right in and update as you go! New Roof & New Septic, the big updates are already done. The Detached Garage needs a new roof and renovations.

  Nancy LaBarbera Keller Williams Hudson Valley

  8 Hill Rd, Middletown, NY 10941
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  /42

  $349,000

  • 4 Beds
  • 1 Bath
  • 1,790 Sq Ft

  38 Prospect St, Middletown, NY 10940

  Welcome to this charming well maintained 1900's Colonial centrally located to everything Middletown has to offer such as schools, walking distance to the Elk's Club, YMCA and Downtown Middletown finest eateries and breweries!, shopping and public transportation. When you arrive to the property the large porch will great you and once you step inside you will notice the old charm starting with

  Pedro Garcia Curasi Realty, Inc.

  38 Prospect St, Middletown, NY 10940
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  /30

  $319,000

  • 3 Beds
  • 1 Bath
  • 1,124 Sq Ft

  82 Houston Ave, Middletown, NY 10940

  Tucked on a dead-end street, this updated 3-bedroom, 1-bath home offers a welcoming blend of character and modern comfort. The cozy living room sets the tone - perfect for everyday living and casual entertaining. A traditional layout flows into a dedicated dining area and an updated kitchen with direct access to a private outdoor space this is ideal for year-round grilling and low-maintenance

  Wendy Beck Krumpfer Realty Group, LLC

  82 Houston Ave, Middletown, NY 10940
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  /44

  $324,999

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  20 Benton Ave, Middletown, NY 10940

  Discover the potential in this charming 3-bedroom, 2-full-bath two-story home with 1,504 sq ft of living space. Full of character and solid construction, this property offers a formal dining room and plenty of room to grow with a full unfinished attic and full, unfinished, walk-out basement featuring washer/dryer hookups.Featuring strong bones and charming original touches, this home is

  Vincent Reda Keller Williams Realty

  20 Benton Ave, Middletown, NY 10940
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  /24

  $349,999

  • 2 Beds
  • 1 Bath
  • 736 Sq Ft

  128 Kleis Road Spur, Middletown, NY 12430

  Welcome to Your Catskills Retreat at 128 Kleis Road SpurTucked away on a quiet spur road and surrounded by evergreens, this charming single-level cabin blends cozy comfort with outdoor living.Relax on the spacious deck, soak in the private hot tub, or gather by the fire pit under the stars. Inside, enjoy an open layout with large windows, a stone fireplace, and sliders to the deck—perfect

  Michelle Andzel Graziano Four Seasons Sotheby's International Realty

  128 Kleis Road Spur, Middletown, NY 12430
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  /14

  $349,000

  • 3 Beds
  • 1.5 Baths
  • 1,604 Sq Ft

  1 Chancery Mews, Middletown, NY 10940

  Welcome to this spacious and well-maintained contemporary-style home located in the sought-after Canterbury Knolls community. Featuring 3 bedrooms, 2 bathrooms, this home offers comfortable and functional living for today’s modern lifestyle. The inviting living room includes a cozy fireplace, while sliding glass doors lead to a private patio—perfect for entertaining or enjoying peaceful evenings

  Sean Walker Keller Williams Realty

  1 Chancery Mews, Middletown, NY 10940
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  /27

  $349,990

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft

  9 Genung St, Middletown, NY 10940

  Charming two-story home in the heart of Middletown! This spacious residence offers a welcoming front porch, perfect for relaxing evenings, and a practical layout filled with natural light. The home features multiple bedrooms, ample living space, and a generous yard with off-street parking. Located in a convenient neighborhood close to schools, shopping, dining, and major highways, this property

  Anthony Rivas Keller Williams Hudson Valley

  9 Genung St, Middletown, NY 10940
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  /10

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  64 Wawayanda Ave, Middletown, NY 10940

  FULLY AVAILABLE AND MOVE IN READY! 3 bedroom, 2 full bath home in a great commuter location. Home offers species kitchen with quartz counter tops & stainless steel appliances. Bright Living room, large tile baths, light fixtures and hardwood floors throughout. Cozy master bedroom with 2 closets and private bath located on the 2st floor. 2 other bedrooms and a full bath is located on main floor.

  Nathan Landau Loop Realty Inc

  64 Wawayanda Ave, Middletown, NY 10940
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  /19

  $379,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  1 Chestnut St, Middletown, NY 10940

  A must see home! This beautiful corner lot home has everything brand new inside - from the windows, closed porch, all walls with plumbing and electrical lines, kitchen with brand new cabinets, countertops and appliances: refrigerator, oven/range, microwave and dishwasher, beautiful bathrooms with tiles, - all NEW. Featuring 3 bedrooms and 2 full bathrooms. It has a great size yard for your summer

  Anita S. Cristiano HomeSmart Homes & Estates

  1 Chestnut St, Middletown, NY 10940
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  /28

  $305,000

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  111 Apple Lane Dr, Middletown, NY 10940

  Picked just for you is this adorable home on Apple Lane! From the moment you walk in, you’ll be greeted by a delightful blast from the past — knotty pine paneling, hardwood floors and an original kitchen complete with metal cabinets and whimsical upper metal cupboards with sliding glass doors that scream mid-century character. Whether you’re a fan of retro style or ready to put your modern touch

  Patricia Sassi RE/MAX Benchmark Realty Group

  111 Apple Lane Dr, Middletown, NY 10940
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  /5

  $300,000

  • Land
  • 7 Acres
  • $42,857 per Acre

  2024 Mount Hope Rd, Middletown, NY

  Looking to build? Land available in prime location. Situated directly between Middletown and Town of Mount Hope with easy access to all major roadways. Zoned for residential and agriculture. Buyer/builder to subdivide 5-8 acres from this 37+ acre parcel as agreeable to seller and proposed in contract. Flat, open, cleared land may be suitable for 1-3 building lots. Land to purchase provides

  Amanda Ferrantello Hudson Valley Griffith

  2024 Mount Hope Rd, Middletown, NY
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  /44

  $385,000

  • 4 Beds
  • 2 Baths
  • 1,634 Sq Ft

  100 Academy Ave, Middletown, NY 10940

  WELCOME HOME!!! A lovely and spacious single family property, with an extra large backyard, located in the center of Middletown is looking for its new owners, ready to move in!!!The house features a total of 4 bedrooms, 2 full baths, plus a office room, with a semi finished basement for laundry and storage. New SS washer dryer included! The 1st floor consists of a nice kitchen with

  Mordy Abelesz eXp Realty

  100 Academy Ave, Middletown, NY 10940
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  /30

  $374,999

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft

  5 Mills Ave, Middletown, NY 10940

  LOCATION, LOCATION, LOCATION! Don’t miss this charming 3 Bedroom, 1.5 Bathroom Two-Story Home located in the heart of Middletown and within the Middletown School District. This home offers unbeatable convenience—just minutes from local restaurants, shopping centers, banks, healthcare facilities, and postal services. Situated close to elementary and secondary schools, and just blocks from Orange

  Richard Baxter Keller Williams Realty

  5 Mills Ave, Middletown, NY 10940
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  /34

  $339,900

  • 3 Beds
  • 2.5 Baths
  • 1,919 Sq Ft

  110 Deer Ct Dr, Middletown, NY 10940

  BACK ON THE MARKET! Welcome to 110 Deer Court Drive, a bright and well maintained 3-bedroom, 2.5-bath unit in the highly sought-after Deer Run community in Middletown, NY. This inviting home features a spacious open floor plan filled with natural light, perfect for both everyday living and entertaining. The living room offers a cozy wood-burning fireplace while the separate dining area flows

  Patricia Sassi RE/MAX Benchmark Realty Group

  110 Deer Ct Dr, Middletown, NY 10940
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  /9

  $395,000

  • 4 Beds
  • 2 Baths

  25 Mill St, Middletown, NY 10940

  Beautifully recently renovated 2 story, with 2 br apartment on second for at $2000./month, which has 2 yr lease, vacant first floor unit with matching new renovation, includes washer and dryer. New kitchen with granite counters, new full tile bath. High efficiency furnaces. First floor is a commercial space, ready to occupy. Tenant pay utilities. Seller says present all offers. Come and

  Mark Tierney Howard Hanna Rand Realty

  25 Mill St, Middletown, NY 10940
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  /8

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft

  2 Rivervale Rd, Middletown, NY 10940

  Charming Corner Townhouse in Middletown – No HOA Fees!Welcome to 2 Riverdale Road, a delightful 3-bedroom, 1.5-bathroom townhouse nestled in the heart of Middletown, NY. This spacious 1,484 sq ft home offers a perfect blend of comfort and convenience, making it an ideal choice for families and first-time homebuyers.Key Features:Spacious Living: Enjoy the warmth of hardwood floors throughout and

  Kilimanjaro Toussaint YourHomeSold Guaranteed Realty

  2 Rivervale Rd, Middletown, NY 10940
• 

  

  /34

  $379,000

  • 3 Beds
  • 1.5 Baths
  • 1,382 Sq Ft

  120 Prospect Ave, Middletown, NY 10940

  Back on market! Buyer lost financing!! What a complete honor to represent this home, the pride of ownership is amazing! Over the last 20 years they have done so many improvements that when you view the home, it will be like they did it last week! When you arrive you will notice the long driveway that leads to a detached garage and nice sized yard. Before you enter the home, put on your

  Pedro Garcia Curasi Realty, Inc.

  120 Prospect Ave, Middletown, NY 10940
• 

  

  /22

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  24 Crescent Place, Middletown, NY 10940

  Attention all investors and home buyers! Look no further, This amazing colonial is in great condition, Features 3 Bedrooms 1 full bathroom, New hot water tank and more... Driveway and garage to accommodate parking and storage, Home is well maintained and move in ready! Great location in town of Middletown and a 90 min drive to NYC! Priced to sell and wont last! Reach out today for your private

  Shlome Weber Q Home Sales

  24 Crescent Place, Middletown, NY 10940
• 

  

  /24

  $329,900

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  9 Fairview Ave, Middletown, NY 10940

  A must see home! This beautiful colonial home will have everything brand new - from the exterior: roof, sidings, windows, porch, deck to the interior: kitchen, all walls with plumbing and electrical lines, kitchen with brand new cabinets, countertops and appliances: refrigerator, oven/range, microwave and dishwasher, beautiful bathrooms with tiles, hardwood floorings - all NEW. Featuring 3

  Anita S. Cristiano HomeSmart Homes & Estates

  9 Fairview Ave, Middletown, NY 10940

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